5-Bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridine-3-sulfonic acid (2-cyclopropylethyl)amide

HRID 1820630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1820630
[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:35])[C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=4[C:31]([F:34])([F:33])[F:32])[CH2:19][CH2:18]3)=[C:14](Br)[CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:35])[C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=4[C:31]([F:34])([F:32])[F:33])[CH2:19][CH2:18]3)=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 112961565-Bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide

Produkt 1

HCID 113640636-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridine-3-sulfonic acid (2-cyclopropylethyl)amideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide (0.100 g, 0.173 mmol) in methanol (5.0 mL) was added Pd/C (0.050 g,12 mol %). The mixture was placed under an atmosphere of hydrogen for 24 hours. The reaction mixture was filtered through celite and concentrated in vacuo. The crude product was purified by column chromatography, eluting with a solvent gradient of 35% ethyl acetate and 65% hexane to yield the desired product (0.020 9, 24%). 1H NMR (300 MHz, CDCl3) δ 8.58-8.57, 7.87-7.83, 7.76-7.71, 7.26-7.23, 7.08-7.04, 6.65-6.62, 4.60-4.56, 4.00-3.93, 3.86-3.64, 3.32-3.28, 3.04-2.97,1.40-1.33, 0.59-0.53, 0.43-0.37, 0.025-0.008. 13C NMR (75 MHz, CDCl3) δ 166.1, 162.6, 159.7, 148.2, 136.7, 129.7, 125.1, 124.7, 116.8, 116.5, 114.9, 114.7, 105.8, 46.5, 44.3, 44.2, 43.4, 41.4, 34.4, 8.2, 4.2. MS (ES+) m/z 501 (M+1).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography
  4. washeluting with a solvent gradient of 35% ethyl acetate and 65% hexane

Quellen und Nachweise

ORD-Eintrag
ord-2ac3a066d21c44cab7c0094e352806ad
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605161B2

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